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Cheap flights from Chicago Midway Airport to Milan from $361

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 4/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
7:25 am - 1:00 pm
MXP
-
MDW
36h 35m
2 stops
$890Multiple Airlines
Thu, Apr 16 - Sun, May 3
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
10:15 am - 1:00 pm
MXP
-
MDW
33h 45m
2 stops
$926Multiple Airlines
Thu, Apr 16 - Sat, Apr 25
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
7:25 am - 1:00 pm
MXP
-
MDW
36h 35m
2 stops
$931Multiple Airlines
Sat, Apr 18 - Sun, May 3
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
4:20 pm - 9:40 am
MXP
-
MDW
24h 20m
2 stops
$939Multiple Airlines
Mon, Apr 27 - Sat, May 9
Multiple Airlines Logo
8:45 am - 9:20 pm
MDW
-
MXP
29h 35m
2 stops
Multiple Airlines Logo
7:00 am - 8:50 pm
MXP
-
MDW
20h 50m
2 stops
$949Multiple Airlines
Wed, Sep 2 - Wed, Sep 9
Multiple Airlines Logo
7:40 am - 11:00 am
MDW
-
MXP
20h 20m
2 stops
Multiple Airlines Logo
7:00 am - 8:10 pm
MXP
-
MDW
20h 10m
2 stops
$951Multiple Airlines
Mon, May 18 - Tue, May 26
Delta Logo
1:59 pm - 11:20 am
MDW
-
LIN
14h 21m
2 stops
Delta Logo
11:00 am - 6:33 pm
LIN
-
MDW
14h 33m
2 stops
$1,252Delta
Tue, May 12 - Fri, May 22
Delta Logo
1:05 pm - 12:00 pm
MDW
-
LIN
15h 55m
2 stops
Delta Logo
6:40 am - 9:46 pm
LIN
-
MDW
22h 06m
2 stops
$1,271Delta
Fri, Aug 21 - Fri, Aug 28
Delta Logo
6:36 pm - 3:55 pm
MDW
-
LIN
14h 19m
2 stops
Delta Logo
6:40 am - 5:56 pm
LIN
-
MDW
18h 16m
2 stops
$1,356Delta
Mon, May 18 - Tue, May 26
KLM Logo
6:36 pm - 3:55 pm
MDW
-
LIN
14h 19m
2 stops
KLM Logo
6:40 am - 5:56 pm
LIN
-
MDW
18h 16m
2 stops
$1,376KLM
Sun, May 10 - Tue, May 26

Air France flights from Chicago Midway Airport to Milan

Our best Air France deals on Chicago Midway Airport to Milan flight tickets
Air France
Aug 10
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$1,116
Air France
Mar 22
MDW6:34 pmChicago Midway
14h 21m
2 stops
MXP2:55 pmMilan Malpensa
Mar 29
MXP11:40 amMilan Malpensa
17h 51m
1 stop
MDW10:31 pmChicago Midway
$2,340
Air France
Mar 22
MDW6:34 pmChicago Midway
14h 21m
2 stops
MXP2:55 pmMilan Malpensa
Mar 29
MXP6:45 amMilan Malpensa
17h 37m
2 stops
MDW5:22 pmChicago Midway
$2,697

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets
Delta
Aug 10
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP6:45 amMilan Malpensa
22h 01m
2 stops
MDW9:46 pmChicago Midway
$1,012
Delta
Aug 10
MDW1:00 pmChicago Midway
14h 25m
2 stops
MXP10:25 amMilan Malpensa
Aug 19
MXP6:45 amMilan Malpensa
16h 42m
2 stops
MDW4:27 pmChicago Midway
$1,016
Delta
Aug 10
MDW10:35 amChicago Midway
15h 50m
1 stop
MXP9:25 amMilan Malpensa
Aug 19
MXP6:45 amMilan Malpensa
18h 46m
2 stops
MDW6:31 pmChicago Midway
$1,061

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Milan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 19, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 4/16

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Sun 5/3

7:25 am-1:00 pm

2 stops36h 35m

$890

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 4/16

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Sat 4/25

10:15 am-1:00 pm

2 stops33h 45m

$926

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 4/18

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Sun 5/3

7:25 am-1:00 pm

2 stops36h 35m

$931

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 4/27

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Sat 5/9

4:20 pm-9:40 am

2 stops24h 20m

$939

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Wed 9/2

8:45 am-9:20 pm

2 stops29h 35m

Milan Malpensa

Wed 9/9

7:00 am-8:50 pm

2 stops20h 50m

$949

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 5/18

7:40 am-11:00 am

2 stops20h 20m

Milan Malpensa

Tue 5/26

7:00 am-8:10 pm

2 stops20h 10m

$951
Quickest round-trip

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Tue 5/12

1:59 pm-11:20 am

2 stops14h 21m

Milan Linate

Fri 5/22

11:00 am-6:33 pm

2 stops14h 33m

$1,252

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Fri 8/21

1:05 pm-12:00 pm

2 stops15h 55m

Milan Linate

Fri 8/28

6:40 am-9:46 pm

2 stops22h 06m

$1,271

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Mon 5/18

6:36 pm-3:55 pm

2 stops14h 19m

Milan Linate

Tue 5/26

6:40 am-5:56 pm

2 stops18h 16m

$1,356

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sun 5/10

6:36 pm-3:55 pm

2 stops14h 19m

Milan Linate

Tue 5/26

6:40 am-5:56 pm

2 stops18h 16m

$1,376

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Sunday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,189. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,365.

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

12h 21m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan takes 12h 21m
There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.
Search flight deals

  • How far is Chicago Midway to Milan by plane?

    Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 12h 21m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Milan?

    Prices for flights from Chicago Midway Airport to Milan are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Milan?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

  • What documentation or ID do you need to fly to Milan?

    The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Menaggio
Brescia
Stresa
Livigno
Levanto
Monza
Assago
Bellano
Lecco
Crema
Rho
Domodossola
Cernobbio
Moltrasio
Bormio
Saronno
Baveno
Novara

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport